🎨 The lost art of dreams

Resetting what we want and daring to name a dream

Last week, I did a terribly Millennial thing:

I got rid of all of my furniture, donated 80% of my clothes, ditched my apartment in San Francisco, and quit my corporate job — all to pursue a creative “calling.”

My parents received the same courtesy of notice on my plans to imminently join them, as my employer received on my plans to imminently leave them.

2 weeks should do the trick?

Flowers sent on my final day by wonderful people in my life: friends and co-workers

Thankfully, my parents obliged — allowing me to use their guest room as an intermittent home base and exceptionally well-priced (free) public storage unit before I hop around the world to “eat, pray, love” and “find myself.”

So long as I don’t start exhibiting alarmingly ~crunchy~ behavior, of course: vomiting advise from a book I only skimmed on how to unblock your Chi and aggressively pushing them to purchase my newly minted set of “healing” crystals like some tweaked out spiritual dealer.

Check back in 2 weeks though, and we’ll see where we’re at.

In all seriousness — I pride myself on being methodic about most decisions, which is why the cliché of this all makes me cringe. And I am definitely not anti-corporate, even though 9-to-5 bashing has remained popular clickbate on every social platform for the past 10 years.

In fact, I really liked my corporate job in Tech. I admired the leaders around me, I was deeply challenged by the work, and I was proud of what I had achieved. I went from being a junior-level operations analyst at my company — bumbling to troubleshoot customer support tickets— to being the Chief of Staff for an engineering org of more than 800 people, managing multi-figure investment tradeoffs against an even bigger multi-figure budget. And I did it in under 5 years.

I felt really good about that. And more importantly: I never would have had the courage to pursue a creative calling if I hadn’t learned what it takes to push myself in a fast-paced tech company. I’m convinced that I couldn’t have gotten that growth anywhere else, and I’m eternally grateful for it.

But then, something changed. Or rather, I changed.

I had proven all that I had set out to prove to myself — “what” I was capable of doing. But the “why” still evaded me, and its absence, scared me. I found myself going through the motions, and fast, but unclear where I wanted the them to take me.

A C-suite member of a Fortune 50? The founder of my own Silicon Valley venture? A management consultant heartily compensated for expert industry advice?

All, worthy dreams. Just not my dream.

And I suspect I’m not the only one that’s slipped into that rut before:

It’s far easier to maintain momentum towards some destination, than to pause and contemplate the destination that you most want.

We all have some fellowship to familiarity, and it can be a sticky one to shake. And even if we sense that our dreams have drifted, it doesn’t always feel worth “reseting” them from scratch and redefining what they are.

Or, worse yet: we know that we never did.

Deep down, that may be the even more unpleasant truth: we know that we never had a North Star — and rather than opening ourselves up to the stakes of long-shots, we intentionally left anything lofty un-named. We intentionally left the canvas of our calling empty, and we implicitly censored our truest dreams from the start.

So I fear that you and me — we did our dreams dirty.

We made the pursuit of dreams a lost art.

Now friend, if you can’t immediately rattle off what your dream pursuit looks like, you may have a dire diagnosis.

You may be ~dreamless.~

It’s a troubling title to own up to, but you’re not alone. I balked at getting the unwelcome badge of dishonor myself.

After all, nobody consciously forsakes their dreams. It’s more that we fudge how we define them. And unfortunately: that’s nearly the same. Our dreams get discounted down to what feels most doable, rather than defined anew.

For me, the pursuit of dreams stopped being a process of “creation” — defining what I wanted most and going after it — and had instead morphed into more of a “calibration” — backing out what I could confidently get, based on the momentum I already had.

So, what would it take to hit the “reset” button on our dreams?

How do we get back to ground truth, and get really honest with ourselves on what we want? How do make sure that we’re not discounting what we most want by force-fitting to what’s familiar?

A humble suggestion: do not immediately rage quit your job.

Instead, consider doing this:

1. Unblock the naming of an authentic dream aloud.

2. Pursue it in parallel to validate your desire for it

3. And only once you have strong conviction, consider doubling-down

If you’ve never done it before, it’s worthwhile to boop the reset button on your own dreams, and start fresh with a thought exercise:

Without considering other people’s expectations or your own perception of feasibility — what do you dream of doing, achieving or becoming?

And there shouldn’t just be one answer here. If you’re opening up your mind enough, you should come out with a whole list of potential answers to this question across many vectors. Vocations, relationships, skillsets — you name it. Plus, articulating as many as you can aloud only debunks the scariness of the exercise and opens yourself up to more honest conversations with yourself, if nothing else.

And indeed, defining any dream aloud is scary — particularly when it bares no resemblance to the path we’re already pursuing. Admitting a dream aloud to yourself sometimes feels like putting your cowardice on full display: it’s only a reminder of all we’re not doing to pursue them.

But, allowing your dreams to remain undefined is a tactic of fear, and a brilliant one at that:

Allowing your dreams to drift un-named is a defense mechanism: you can’t fall short on something you never start, or disappoint yourself on something you never admit to want.

Yikes.

So, if you sense in some teeny-tiny part of you that you might be bending the truth on your dreams because of some gaps in self-belief, consider digging into the root cause rather than fervently covering it up.

I think there’s a few ways that can one end up unable to name their own dream aloud. For me, it was some combination of the following:

• Reward Rationalization: The rewards of your current path are widely celebrated and objectively rewarded. So, it becomes easy to rationalize away the appetite for anything else when it comes at a high opportunity cost. Sure — there’s some curiosity for something different, that you’d really love to quell — but you’ve got something certain already in-hand! Don’t get greedy now dreaming for all of that greatness in something different, lest you sacrifice all the perks of a stable precedent.

• Daily Distraction: You don’t crave anything else. You’re content. Or, at least, the daily distractions have done a splendid job drowning out any voice of desire for something different. Same-same, right? You know this isn’t what you adore, but you’d be hard pressed to come up with what you do. You’d rather wander in the abstract from afar, than sign up for any real work.

• Self-Doubt: You have in mind what you’d like to pursue, but the comfort of being wildly successful at some thing overpowers the curiosity for the thing. You can’t bare the prospect of trying hard at something for a long time, and still coming up short. And deep down, you just don’t trust that you can make what you dream of a reality.

There’s no easy way to debunk these, other than for you to sit with them and realize that they all stem from fear. And the goal of the exercise isn’t to magically deconstruct that fear — that’s tremendously difficult to do (and if you do manage to do that, by all means, help ya girl out and send some sage words this way!).

Rather: the goal is to just get sick of it. Track down where the fear lives in the root causes above, get pissed off that it’s still hanging around rent-free, and just shut it up for a few minutes by duck taping its mouth closed if you can’t easily evict it.

Just long enough to make authentic desire audible in your own mind, for an open discussion with yourself on your truest dreams.

Once you’ve got an authentic dream in mind, rage quitting your job starts to look like an awfully alluring ~mic-drop~ moment.

But, that spicy desire is sometimes seeded by the wrong thing:

You need to make sure that when you choose to make a major pivot in pursuit of a dream, that it’s a decision being made from a place of deep intuition for what you want, and not escapism from what you don’t want.

And it’s too easy to confuse the two, particularly if you feel downright miserable in your job. I almost quit 1 year into mine — and not because ~I wanted to pursue my dream of being a professional writer!

There were some clues that this could be a full-blown calling. But I had nowhere near enough conviction yet. And more than that: I knew that my desire to jump ship was driven more by the self-doubt that I had in my current job, as a green recent graduate.

So while I knew I could easily sell other people on some story to quit my job to take a leap of faith! — I couldn’t sell myself on that truth. I’d always secretly know that I had scurried away out of fear of inadequacy.

And if that resonates even slightly with you, it’s important to identify now: because your capacity for grit in one domain, is transferable to others. And the inverse is equally true:

If self-doubt is riddling your existing day job, there’s a good chance that it will also throw a rut in your ability to define and bravely pursue an alternate dream.

Bottom line: I’m glad I didn’t quit my job a day earlier.

Because while it would have looked ~bold and brave~ from afar, it would have kicked the can on shaping resilience that needed to be done on myself no matter what I chose to do. The hardest thing — but the right thing — was to not quit my job prematurely.

Instead, for 4 years, I worked through the self-doubt in my day job. And in waking moments outside of work, I wrote — building the confidence that I could, and pressure testing conviction that the dream was a pursuit I genuinely longed for, and not a loophole out of something else.

Writing outside of work; well-fueled by cappuccinos and chocolate muffins

So consider this: redirect each baby step forward in self-belief that you tackle in your day job, into self-belief in your ability to tackle any job. And use that to incrementally pursue your dream in parallel. When you have full confidence that the idea of pursuing something new has nothing to do with escaping the old, only then, consider taking the plunge.

So yea. It took my literal years of writing in parallel to a full-time job to pressure test if this dream was genuine. From all that time and toil of juggling the two in parallel, I’ve gotten precisely 2 additional subscribers to my blog and 200 more frown-lines on my face from re-writes to my work-in-progress manuscript.

Bummer, given Botox apparently ain’t cheap and I’m now technically unemployed.

But even in all the uncelebrated suffering work of writing in solitude, I can attest to the following: the satisfaction we get from pursuing our dreams is not a binary output, based strictly on “achievement” of the dream.

And if you think the joy of dreams can only be realized as “all” or “nothing” — it’s no surprise that the weighted average of that risk has many of us backing out to begin with.

Instead, if we want to actually muster the might to take a bolder plunge, we must choose to believe something different:

We need to believe that the delight to be gained in the “art” of dreams isn’t strictly in the final artwork — it’s in the art work.

The craftsmanship. The process. The pursuit. And you may not necessarily feel that from day 1. For lack of a better word: you may just need to take it on “faith.”

But once you do start, you may be surprised: the mere satisfaction of your own intentionality feels good. And delightful, unexpected outcomes — perhaps different and incremental to the original intended outcome— are probably more evenly distributed throughout the journey than one would have expected.

So taking action to start a dream requires anchoring your mindset on a belief:

Satisfaction from your dream is a spectrum that you can start dialing up today, by merely starting today.

And I cannot emphasize that enough.

You must choose to believe that in your bones if you’re going to get over the overwhelming feeling of doubling down: over the long-run, it will feel better to start something right, and shoot to achieve even some of it, rather than stick to something wrong, even if you achieve all of it.

There’s a lot of reasons that I believe “art” is an apt analogy for dreams.

For one thing: art is non-objective, and often, controversial.

What you adore, others despise. What you detest, others faun over. Dreams, like art, cannot be universally understood, and that’s a big part of what makes it so hard to pursue them at times: the world relies on systems to organize collective action. And systems rely on some agreement — objective consensus for what action makes sense.

So when we have such divergence in the nature of dreams across individuals, it’s hard to set up a social system that universally celebrates them. That’s why more money — the most objective mechanism we have — readily becomes a deciding factor for most people’s dreams.

And to choose to pursue dreams in the absence of shared consensus, requires accepting that you will not be celebrated publicly. Perhaps for a very long time. Or perhaps, ever.

At its core, art is about appreciation for what the artist loves, and honoring that, without harboring ill-will towards other forms of self-expression.

The art of dreams doesn’t concern itself with cynicism for the choices that other people are making, or spite for important structures that allow the world to function. It’s not about sticking it to the man! Or, ditching society’s expectations!

If you end up needing to drop something else to honor the art of dreams, like I did — that’s okay. But at its core: it should be about celebrating you in some small way, whether the world ends up joining in or not.

And that’s what I love most about the art of dreams: in a world of billions of people, with all the social structures and systems that are indeed necessary to organize it, a dream is wonderfully freeform and entirely yours. It cannot be dictated by anyone else. And it may the most “you” part of you that there is.

Perhaps that’s what we’ve always meant by “finding ourselves.”

It’s finding the courage to stay open minded and creative, as an artist of your life at every phase of it — whether that’s as a green 22-year old new grad, or a 75-year old retiree — and even if no one understands your art.

You are the creator and you are the critic.

It’s art if you say it’s art. It’s done when you say it’s done. And it’s delightful if you say it’s delightful.

So dear artist, consider allowing yourself to throw the sheet off of that empty canvas, mix a few colors on your palette and perhaps, start small: a few brush strokes as baby steps towards your dream — no matter what that dream is.

Because it’s a worthy dream, if you dare to claim it.

And I suspect, surprisingly doable, as soon as you choose to start it.

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